diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 9d88667111ce5..8e24fee20606d 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -27037,8 +27037,8 @@ namespace ts {
             return node === conditional.whenTrue || node === conditional.whenFalse ? getContextualType(conditional, contextFlags) : undefined;
         }
 
-        function getContextualTypeForChildJsxExpression(node: JsxElement, child: JsxChild) {
-            const attributesType = getApparentTypeOfContextualType(node.openingElement.tagName);
+        function getContextualTypeForChildJsxExpression(node: JsxElement, child: JsxChild, contextFlags?: ContextFlags) {
+            const attributesType = getApparentTypeOfContextualType(node.openingElement.tagName, contextFlags);
             // JSX expression is in children of JSX Element, we will look for an "children" attribute (we get the name from JSX.ElementAttributesProperty)
             const jsxChildrenPropertyName = getJsxElementChildrenPropertyName(getJsxNamespaceAt(node));
             if (!(attributesType && !isTypeAny(attributesType) && jsxChildrenPropertyName && jsxChildrenPropertyName !== "")) {
@@ -27057,28 +27057,28 @@ namespace ts {
             }, /*noReductions*/ true));
         }
 
-        function getContextualTypeForJsxExpression(node: JsxExpression): Type | undefined {
+        function getContextualTypeForJsxExpression(node: JsxExpression, contextFlags?: ContextFlags): Type | undefined {
             const exprParent = node.parent;
             return isJsxAttributeLike(exprParent)
-                ? getContextualType(node)
+                ? getContextualType(node, contextFlags)
                 : isJsxElement(exprParent)
-                    ? getContextualTypeForChildJsxExpression(exprParent, node)
+                    ? getContextualTypeForChildJsxExpression(exprParent, node, contextFlags)
                     : undefined;
         }
 
-        function getContextualTypeForJsxAttribute(attribute: JsxAttribute | JsxSpreadAttribute): Type | undefined {
+        function getContextualTypeForJsxAttribute(attribute: JsxAttribute | JsxSpreadAttribute, contextFlags?: ContextFlags): Type | undefined {
             // When we trying to resolve JsxOpeningLikeElement as a stateless function element, we will already give its attributes a contextual type
             // which is a type of the parameter of the signature we are trying out.
             // If there is no contextual type (e.g. we are trying to resolve stateful component), get attributes type from resolving element's tagName
             if (isJsxAttribute(attribute)) {
-                const attributesType = getApparentTypeOfContextualType(attribute.parent);
+                const attributesType = getApparentTypeOfContextualType(attribute.parent, contextFlags);
                 if (!attributesType || isTypeAny(attributesType)) {
                     return undefined;
                 }
                 return getTypeOfPropertyOfContextualType(attributesType, attribute.name.escapedText);
             }
             else {
-                return getContextualType(attribute.parent);
+                return getContextualType(attribute.parent, contextFlags);
             }
         }
 
@@ -27272,10 +27272,10 @@ namespace ts {
                 case SyntaxKind.ExportAssignment:
                     return tryGetTypeFromEffectiveTypeNode(parent as ExportAssignment);
                 case SyntaxKind.JsxExpression:
-                    return getContextualTypeForJsxExpression(parent as JsxExpression);
+                    return getContextualTypeForJsxExpression(parent as JsxExpression, contextFlags);
                 case SyntaxKind.JsxAttribute:
                 case SyntaxKind.JsxSpreadAttribute:
-                    return getContextualTypeForJsxAttribute(parent as JsxAttribute | JsxSpreadAttribute);
+                    return getContextualTypeForJsxAttribute(parent as JsxAttribute | JsxSpreadAttribute, contextFlags);
                 case SyntaxKind.JsxOpeningElement:
                 case SyntaxKind.JsxSelfClosingElement:
                     return getContextualJsxElementAttributesType(parent as JsxOpeningLikeElement, contextFlags);
diff --git a/tests/baselines/reference/contextuallyTypedJsxAttribute.js b/tests/baselines/reference/contextuallyTypedJsxAttribute.js
new file mode 100644
index 0000000000000..18b4dec211ccc
--- /dev/null
+++ b/tests/baselines/reference/contextuallyTypedJsxAttribute.js
@@ -0,0 +1,32 @@
+//// [index.tsx]
+interface Elements {
+  foo: { callback?: (value: number) => void };
+  bar: { callback?: (value: string) => void };
+}
+
+type Props<C extends keyof Elements> = { as?: C } & Elements[C];
+declare function Test<C extends keyof Elements>(props: Props<C>): null;
+
+<Test
+  as="bar"
+  callback={(value) => {}}
+/>;
+
+Test({
+  as: "bar",
+  callback: (value) => {},
+});
+
+<Test<'bar'>
+  as="bar"
+  callback={(value) => {}}
+/>;
+
+
+//// [index.jsx]
+<Test as="bar" callback={function (value) { }}/>;
+Test({
+    as: "bar",
+    callback: function (value) { }
+});
+<Test as="bar" callback={function (value) { }}/>;
diff --git a/tests/baselines/reference/contextuallyTypedJsxAttribute.symbols b/tests/baselines/reference/contextuallyTypedJsxAttribute.symbols
new file mode 100644
index 0000000000000..fb315569a7eda
--- /dev/null
+++ b/tests/baselines/reference/contextuallyTypedJsxAttribute.symbols
@@ -0,0 +1,68 @@
+=== tests/cases/compiler/index.tsx ===
+interface Elements {
+>Elements : Symbol(Elements, Decl(index.tsx, 0, 0))
+
+  foo: { callback?: (value: number) => void };
+>foo : Symbol(Elements.foo, Decl(index.tsx, 0, 20))
+>callback : Symbol(callback, Decl(index.tsx, 1, 8))
+>value : Symbol(value, Decl(index.tsx, 1, 21))
+
+  bar: { callback?: (value: string) => void };
+>bar : Symbol(Elements.bar, Decl(index.tsx, 1, 46))
+>callback : Symbol(callback, Decl(index.tsx, 2, 8))
+>value : Symbol(value, Decl(index.tsx, 2, 21))
+}
+
+type Props<C extends keyof Elements> = { as?: C } & Elements[C];
+>Props : Symbol(Props, Decl(index.tsx, 3, 1))
+>C : Symbol(C, Decl(index.tsx, 5, 11))
+>Elements : Symbol(Elements, Decl(index.tsx, 0, 0))
+>as : Symbol(as, Decl(index.tsx, 5, 40))
+>C : Symbol(C, Decl(index.tsx, 5, 11))
+>Elements : Symbol(Elements, Decl(index.tsx, 0, 0))
+>C : Symbol(C, Decl(index.tsx, 5, 11))
+
+declare function Test<C extends keyof Elements>(props: Props<C>): null;
+>Test : Symbol(Test, Decl(index.tsx, 5, 64))
+>C : Symbol(C, Decl(index.tsx, 6, 22))
+>Elements : Symbol(Elements, Decl(index.tsx, 0, 0))
+>props : Symbol(props, Decl(index.tsx, 6, 48))
+>Props : Symbol(Props, Decl(index.tsx, 3, 1))
+>C : Symbol(C, Decl(index.tsx, 6, 22))
+
+<Test
+>Test : Symbol(Test, Decl(index.tsx, 5, 64))
+
+  as="bar"
+>as : Symbol(as, Decl(index.tsx, 8, 5))
+
+  callback={(value) => {}}
+>callback : Symbol(callback, Decl(index.tsx, 9, 10))
+>value : Symbol(value, Decl(index.tsx, 10, 13))
+
+/>;
+
+Test({
+>Test : Symbol(Test, Decl(index.tsx, 5, 64))
+
+  as: "bar",
+>as : Symbol(as, Decl(index.tsx, 13, 6))
+
+  callback: (value) => {},
+>callback : Symbol(callback, Decl(index.tsx, 14, 12))
+>value : Symbol(value, Decl(index.tsx, 15, 13))
+
+});
+
+<Test<'bar'>
+>Test : Symbol(Test, Decl(index.tsx, 5, 64))
+
+  as="bar"
+>as : Symbol(as, Decl(index.tsx, 18, 12))
+
+  callback={(value) => {}}
+>callback : Symbol(callback, Decl(index.tsx, 19, 10))
+>value : Symbol(value, Decl(index.tsx, 20, 13))
+
+/>;
+
diff --git a/tests/baselines/reference/contextuallyTypedJsxAttribute.types b/tests/baselines/reference/contextuallyTypedJsxAttribute.types
new file mode 100644
index 0000000000000..6e33aa57d8253
--- /dev/null
+++ b/tests/baselines/reference/contextuallyTypedJsxAttribute.types
@@ -0,0 +1,66 @@
+=== tests/cases/compiler/index.tsx ===
+interface Elements {
+  foo: { callback?: (value: number) => void };
+>foo : { callback?: (value: number) => void; }
+>callback : (value: number) => void
+>value : number
+
+  bar: { callback?: (value: string) => void };
+>bar : { callback?: (value: string) => void; }
+>callback : (value: string) => void
+>value : string
+}
+
+type Props<C extends keyof Elements> = { as?: C } & Elements[C];
+>Props : Props<C>
+>as : C
+
+declare function Test<C extends keyof Elements>(props: Props<C>): null;
+>Test : <C extends keyof Elements>(props: Props<C>) => null
+>props : Props<C>
+>null : null
+
+<Test
+><Test  as="bar"  callback={(value) => {}}/> : error
+>Test : <C extends keyof Elements>(props: Props<C>) => null
+
+  as="bar"
+>as : "bar"
+
+  callback={(value) => {}}
+>callback : (value: string) => void
+>(value) => {} : (value: string) => void
+>value : string
+
+/>;
+
+Test({
+>Test({  as: "bar",  callback: (value) => {},}) : null
+>Test : <C extends keyof Elements>(props: Props<C>) => null
+>{  as: "bar",  callback: (value) => {},} : { as: "bar"; callback: (value: string) => void; }
+
+  as: "bar",
+>as : "bar"
+>"bar" : "bar"
+
+  callback: (value) => {},
+>callback : (value: string) => void
+>(value) => {} : (value: string) => void
+>value : string
+
+});
+
+<Test<'bar'>
+><Test<'bar'>  as="bar"  callback={(value) => {}}/> : error
+>Test : <C extends keyof Elements>(props: Props<C>) => null
+
+  as="bar"
+>as : "bar"
+
+  callback={(value) => {}}
+>callback : (value: string) => void
+>(value) => {} : (value: string) => void
+>value : string
+
+/>;
+
diff --git a/tests/cases/compiler/contextuallyTypedJsxAttribute.ts b/tests/cases/compiler/contextuallyTypedJsxAttribute.ts
new file mode 100644
index 0000000000000..1510e7ef44c09
--- /dev/null
+++ b/tests/cases/compiler/contextuallyTypedJsxAttribute.ts
@@ -0,0 +1,26 @@
+// @jsx: preserve
+// @noImplicitAny: true
+
+// @filename: index.tsx
+interface Elements {
+  foo: { callback?: (value: number) => void };
+  bar: { callback?: (value: string) => void };
+}
+
+type Props<C extends keyof Elements> = { as?: C } & Elements[C];
+declare function Test<C extends keyof Elements>(props: Props<C>): null;
+
+<Test
+  as="bar"
+  callback={(value) => {}}
+/>;
+
+Test({
+  as: "bar",
+  callback: (value) => {},
+});
+
+<Test<'bar'>
+  as="bar"
+  callback={(value) => {}}
+/>;